Looking to Break the Siege: George Washington at Cambridge

A 1900s print showing the exterior view of the Longfellow House - Washington's Headquarters from the street on a winter's day.

McLoughlin Brothers, 1904. Library of Congress

The Siege Drags On

By October 1775, the Siege of Boston had dragged on for months. British troops remained entrenched in the city, while the Continental Army held positions in the surrounding areas. The fighting had slowed, but the war had not. From his headquarters in Cambridge, Commander George Washington faced a difficult truth: the siege alone would not force the British out. As winter approached, he had to decide how to break the deadlock or endure it.

Proposals to Break the Deadlock

Washington proposed several plans to break the siege during the winter, but his war council rejected the plans. He agreed to delay an attack "for the present at least."^[1] Ultimately, Washington had to wait until he could replenish the Continental Army’s ranks and secure sufficient artillery and weapons before attempting to break the siege.

The weapons and artillery needed to fortify the siege lines around Boston were being transported to Cambridge from Fort Ticonderoga in New York by Henry Knox, whom Congress had appointed Colonel of the Regiment of Artillery in December 1775.^[2] While waiting for Knox and his artillery company, Washington and his generals focused on rebuilding the army and strategizing where new fortifications would most threaten the British in Boston.

Breaking the siege proved to be only one of Washington’s concerns. As temperatures dropped, the cold weather brought new challenges. Supplies ran low. Soldiers lacked adequate clothing and shelter.^[3] Disease spread through the camps. At the same time, Washington worked to transform a collection of disorderly and discontent militia units into a disciplined, unified army capable of action.^[4]

Shelter, Sickness, and Survival

After taking command of the army, Washington sought to fortify the area surrounding Boston. This included the construction of barracks along the siege lines in Cambridge, Brookline, Roxbury, and Dorchester.^[5] As winter approached, construction accelerated to replace tents with more durable shelter. Even so, soldier Daniel Granger described the barracks as, "not so warm & comfortable: the Barraks [sic] were hastily built only boarded & battened & without Windows excepting a square opening with a sliding shutter."^[6]

Despite regular inspections for cleanliness, the cold coupled with lack of food supplies led to rising illness. Deaths from typhus, smallpox, and dysentery were not uncommon.^[7] Soldier Moses Sleeper captured the bleak reality of the situation in his war diary: "Monday Decem 25 Christmas Verry [sic] dull Christmas nothing to Eat nor drink to work on [Barracks]."^[8] Ensuring the troops had enough food rations, proper clothing, and adequate blankets and shelter remained an ongoing struggle for Washington throughout the war, and these shortages took a measurable toll on morale and reenlistment.

View of siege lines in Roxbury, south of Boston. From Archibald Robertson's diaries and sketches in America (1762-1780).

Spencer Collection, The New York Public Library. "No. 2. View of the neck & lines at Boston with the rebel works at Roxburgh" The New York Public Library Digital Collections.

Morale and Enlistment Issues

Throughout the fall and early winter, Washington issued orders to stabilize his forces. Revolutionary War orderly books from December 1775 through January 1776, kept at Roxbury by John Bailey’s Regiment under General Artemas Ward, record directives concerning the enlistment of new troops and the reenlistment of those already in service. Most soldiers’ enlistment terms were set to expire at the end of December, and Washington and his generals worried that many would choose not to reenlist. In addition to inadequate supplies and shelter, Washington also struggled to ensure the men were paid on time, all of which potentially contributed to low reenlistment rates.

Washington also combated serious discipline problems. He worried the army’s behavior reflected poorly on the cause itself, writing of "The Honour & Credit of the Colony which has been Wounded by the Restles[s] and Disobeadinte [sic] Conduct of Some of its own Sons."^[9] For example, soldiers deserted or defected across British lines,^[10] officers ordered lashings for unruly behavior, and soldiers faced court-martial for offenses including "insolent and abusive language and acting unbecoming of an officer."^[11]

To address these issues, Washington emphasized training and vigilance. Division orders from December 12 stressed the proper instruction of new soldiers, directing officers to:

"Take care to instruct the new militia in the Common Methods of the camp in general. As to duty; and in particular that they be acquainted with the general order, concern that no imprudence may happen by such neglect."

Further orders from Cambridge on December 13 outlined how with proper oversight the men "will become agreeable rather then a burdthen [sic]." These measures carried urgency, as disorder could invite harm or signal weakness to British observers.^[12]

A scanned page from the orderly book of John Bailey's Regiment, Continental Army, December 12, 1775.

Massachusetts Historical Society

An Army Reforms as the Siege Holds

During this time, Washington and delegates from the Continental Congress, along with leaders from the New England colonies, developed a plan for reorganizing the army. On January 1, 1776, Washington formally announced the army’s reorganization. He also issued a new set of rules and regulations, reminding his officers and soldiers that "an Army without Order, Regularity & Discipline, is no better than a Commission’d Mob."^[13]

However, many soldiers who had chosen not to reenlist left when their enlistments expired. Anticipating this loss, Washington issued orders pushing for those "who have their Countries welfare so much at heart as to stay till the last of January next if Necessary" to join newly established regiments, while directing officers to collect ammunition from departing troops for redistribution.^[14]

While the restructuring brought cohesion, Washington recognized that the loss of experienced soldiers brought additional concerns. This, combined with shortages of arms and ammunition, left the army exposed to nearby British forces. These challenges continued to delay any significant movement to drive out the British.

A partial map of Boston with its environs in 1775 and 1776 showing Washington's headquarters at Cambridge in the upper left and the Continental Army's fortifications surrounding Boston.

Digital Commonwealth, Massachusetts Collections Online

Preparing to Break the Siege

Although the British did not attack during this period of transition, a January 4 letter from Washington to John Hancock reveals his eagerness to act and asks for Hancock’s and Congress’ patience while waiting for the means to do so:

"I beg the favour of you Sir, to assure Congress, shall be attempted to be put in execution, the first moment I see a probability of success, and in such a way, as a Council of Officers shall think most likely to produce it; but if this should not happen as soon as you may expect, or my wishes prompt to, I request that Congress will be pleased to Advert to my situation, and do me the justice to beleive [sic], that circumstances, & not want of inclination, are the cause of delay"^[15]

Meanwhile, Washington tracked the slow progress of Henry Knox and the train of artillery while preparing the army to put the weapons to use when they arrived. Once Knox finally reached Cambridge at the end of January, Washington felt he had the supplies needed to force the British out of Boston.

On February 16, 1776, George Washington met again with his officers in Cambridge to consider a direct assault on Boston. Washington believed a decisive strike might end the siege, especially before expected British reinforcements arrived. He reported that the Continental Army had nearly 9,000 soldiers fit for duty, with more militia arriving, but their supply of powder was dangerously low. Without enough ammunition to support artillery, the army would have to rely mainly on small arms.

The generals concluded that an assault was still too risky. They believed British forces, well supported by artillery and the naval fleet, were stronger than estimates suggested, and the Continental Army still lacked enough soldiers and arms for an offensive attack. If colonial forces assaulted the town, they agreed it would require several days of bombardment, something they could not attempt without more powder.^[16]

The council resolved that a cannonade and bombardment would be advisable only after the army secured a proper supply of powder. In the meantime, they agreed to prepare to take possession of Dorchester Heights, hoping to draw the British out of Boston. Rather than launch a costly assault, Washington and his generals chose a position that would force the enemy to respond.

By holding his forces together through the coldest months of the siege, Washington preserved the army and positioned it for action. The plans he formed during that winter allowed him and his council to move swiftly to fortify Dorchester Heights, setting the stage for the Evacuation of Boston and the end of British occupation on March 17, 1776.

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Footnotes

[1] David McCullough, 1776 (New York: Simon & Schuster, 2006), 53.

[2] "Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776," Reel I, Volume 1. Revolutionary War Orderly Books, Massachusetts Historical Society.

[3] "George Washington’s Cambridge Headquarters," Longfellow House Washington's Headquarters National Historic Site, National Park Service, last updated September 25, 2025. Accessed February 17, 2026.

[4] "The Revolutionary War Diary of Moses Sleeper," Longfellow House Washington's Headquarters National Historic Site, National Park Service. Last updated July 2, 2025, accessed February 17, 2026.

[5] "The Revolutionary War Diary of Moses Sleeper."

[6] M. M. Quaife, "A Boy Soldier Under Washington: The Memoir of Daniel Granger," The Mississippi Valley Historical Review, vol. 16, no. 4 (March 1930) pp. 538–60, accessed February 17, 2026.

[7] Elizabeth Fenn, Pox Americana: The Great Smallpox Epidemic of 1775-82 (New York: Hill and Wang, 2001), 50-54; "The Revolutionary War Diary of Moses Sleeper."

[8] "The Revolutionary War Diary of Moses Sleeper."

[9] "Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776."

[10] "The Revolutionary War Diary of Moses Sleeper."

[11] "Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776."

[12] "Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776."

[13] "General Orders, 1 January 1776," Founders Online, National Archives. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988, pp. 1–5.]

[14] "Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776."

[15] "George Washington to John Hancock, 4 January 1776," Founders Online, National Archives. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988, pp. 18–21.]

[16] The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988, 320–324.

Sources

Bell, John L. George Washington’s Headquarters and Home Historic Resource Study. Cambridge, MA: Longfellow House–Washington’s Headquarters National Historic Site, National Park Service, U.S. Department of the Interior, 2012.

Fenn, Elizabeth A. Pox Americana: the Great Smallpox Epidemic of 1775-82. New York: Hill and Wang, 2001.

Frothingham, Richard. History of the Siege of Boston, and of the Battles of Lexington, Concord, and Bunker Hill. Boston: Charles C. Little and James Brown, 1851.

"Generals and Staff at Washington’s Cambridge Headquarters." Longfellow House Washington's Headquarters National Historic Site, National Park Service. Last updated February 20, 2025. Accessed February 17, 2026.

"General Orders, 1 January 1776." Founders Online, National Archives. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988, pp. 1–5.]

"George Washington’s Cambridge Headquarters." Longfellow House Washington's Headquarters National Historic Site, National Park Service. Last updated September 25, 2025. Accessed February 17, 2026.

"George Washington to John Hancock, 4 January 1776." Founders Online, National Archives. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988, pp. 18–21.]

"Henry Knox." National Park Service. Last updated February 20, 2025. Accessed February 17, 2026.

McCullough, David. 1776. New York: Simon & Schuster, 2006.

"The Revolutionary War Diary of Moses Sleeper." Longfellow House Washington's Headquarters National Historic Site, National Park Service. Last updated July 2, 2025. Accessed February 17, 2026.

"Orderly Book of John Bailey’s Regiment, Continental Army (Mass.), 12 December 1775 – 5 January 1776," Reel I, Volume 1. Revolutionary War Orderly Books, Massachusetts Historical Society.

The Papers of George Washington, Revolutionary War Series, vol. 3, 1 January 1776 – 31 March 1776, ed. Philander D. Chase. Charlottesville: University Press of Virginia, 1988.

Quaife, M. M. "A Boy Soldier Under Washington: The Memoir of Daniel Granger." The Mississippi Valley Historical Review, vol. 16, no. 4 (March 1930) pp. 538–60. Accessed February 17, 2026.